A Futile Attempt at Freedom
by Desidero
Summary: Dean and Sam are on the run from Henriksen in their land, accused for many crimes they didn't commit and some they did commit. After being chased for several months they make it to the neighboring country, but only gets a few days of freedom before they are captured by slavetraders. One of the men takes a particular interest in Dean. M/M between Dean/OMC
1. Chapter 1

"Hurry up, Sam!" Dean shouted, as he ran through the tall grass on the large, open field and stopped for a few moments to catch his breath. He cast a short glance behind him, and was relieved when he saw his brother's large body stumble out of the woods and sprint towards him. Their sprint through the thorny branches a few moments ago had ripped up Sam's shirt, and he was covered in dirt and blood from small cuts all over his face and body. He looked like hell, but Dean knew he didn't look much better himself.

Sam ran towards his older brother, but he didn't get the time to take a pause. As soon as he had caught up with him they could hear the sound of hooves and horses in the distance growing stronger, the sound of their pursuers coming closer. The two brothers ran for their lives when the arrows started flying around them, until they reached the end of the field.

The field ended at the ledge of a tall cliff, and far below they could see a deep river flow, the river that signaled the border of the kingdom and freedom. Without hesitation they stripped out of their heaviest clothing and weapons, grabbed each other's hands and with a last look Dean managed to give his younger brother a weak smile, before they both jumped in a hope for freedom.

xxxx

The brothers crawled out of the river half an hour later, and even if they were cold, wet and exhausted they wasted no time in case they had been followed, and ventured deeper into the new land for several hours. When the sun was on its way down for the day they decided to make camp for the night.

It wasn't until they sat around the crackling fire and could feel the warmth spread through their bodies they allowed themselves to relax, and Dean let out a short laugh.

"We made it Sammy. I don't know how, but we actually made it over the border!" Dean said with a smile that was returned by his brother. They had been on the run for several months now, and crossing the border had been their only choice in the end.

"Yeah, I know, but… Are you sure we actually are any safer here? You know how they treat foreigners in this land." Sam said weakly. "And with our luck recently..."

"We don't have a group of men led by Henriksen, who you know was set out to kill us even if it was the last thing he did, to hunt us down in this land. I guess if we stay in the woods, and keep away from any roads and villages we are safe. And in a few years things will probably cool down in our land and we can return home. Or travel further south, to the next land." Dean said with a shrug and tossed a few more branches at their small fire. "Get some rest now Sam, I'll take the first watch."

xxxx

After Sam had fallen asleep, Dean took his time to observe his younger brother's face in the light from their little campfire, like he usually did when Sam was asleep. Sam had always had that young and innocent look, and together with his big brown eyes and the long brown hair he had looked almost like a puppy growing up. But that was before their life on the run, before he was captured and `interrogated´ about his brother's whereabouts. Dean had been in the woods on a hunting trip alone that day, and when he came back in the evening and realized Sam was captured it had been several hours before he found him. His younger brother was bloody and beaten, with deep cuts and slashes all over when Dean arrived. A few of them across his face. The deepest started over the left eyebrow, across the eye, and ended beside his mouth. He would never see with that eye again, and the scars would never disappear from his ruined face.

Dean had killed them all in less than three minutes when he rescued his brother. Each time he looked at his Sam's mauled face, and the eye patch he wore over the destroyed eye, he wanted to kill them all over again. Slow and so painful, he would make them suffer until death was a mercy they welcomed.

xxx

The next day they tried to hunt in the woods. The clothes they had on them was all they owned, but if they could find some of the deer, fox or rabbits they knew ventured these woods, they could get both food for several days and skins for new clothes. Sam had spent the morning crafting a simple hunting bow and a few arrows while Dean removed all traces off their camp. Henriksen could still be after them, Dean doubted the rest of the men had followed them over the border, but Henriksen was crazy enough to do that. He would probably never rest until he knew Dean was dead.

Henriksen believed Dean was a dangerous, crazy rapist, killer and criminal that used witchcraft and worshipped the devil. All because of a man that had come to their village that had looked like a mirrored image of Dean. That man had killed and raped those girls, but since everyone in their village knew Dean, they believed it was he that had done it. Dean had confronted and killed the man that posed like him, but when he showed the dead body to Henricksen to prove his innocence he was instead accused of witchcraft. Henriksen believed Dean had created a demonic copy of himself and ordered it to kill. Dean was captured, but rescued by Sam before he was executed, and they quickly left the village.

After that Dean and Sam was forced to a life on the run, no matter where they went Henriksen and his men followed soon after on their manhunt, and that's why they had no other choice than to leave the country. Dean only hoped some of the stories of what happened to unwelcomed foreigners in this land weren't true. On their journey to the border the brothers had heard many stories from locals of people that had crossed the border and never been heard from again. Only a few people had managed to cross the border and come back again, and they said foreigners were captured and traded as slaves, if they were too old or weak to be used they were simply killed on the spot. Dean and Sam had heard these stories and knew what they risked, but there choice was either dying by Henriksen's hands or maybe living as a slave if they ever were captured, and they both chose life. As long as they were alive, they still had a chance at finding their freedom.


	2. chapter 2

During the morning it started to rain heavily. Dean didn't like this at all, not only did the water soak them from head to toe, it soaked the ground, leaving footsteps and traces after them in the mud they couldn't erase. He just hoped nobody followed them. The rain also made the animals in the forest hide in search for cover, leaving the brothers to gather the food they could find instead of hunting for it. Lucky for them it was late in the summer now, and the woods were full of ripe berries. They stopped to eat every time they came across a patch of blueberries or some bushes with raspberries, and even found an apple tree on a field. The apples were not quite ready yet, they were yellow and sour, but it was food either way. Living on the run for a few months learnt them to eat while they could and what they could.

In the afternoon the rain cleared up and the sun came out from behind the clouds. They came upon a small stream with clear water and took a break to drink some water and relax. The sun was warm now, and Dean laid down on a large rock to let the sun warm him and dry his wet clothes. The clothes they wore could only be called rags now, they both only wore thin shirts, and light pants that were dirty and thorn up, and neither of them had any shoes anymore.

Dean missed the weapons he had to drop before they jumped off the cliff, the sword he had inherited from his father and his hunting bow. They were too heavy, and would have dragged him down in the water. All he had now was the small dagger he had tied to his left leg, and the small slingshot he had tucked in his pants. He looked over to his younger brother and couldn't help but laugh when he saw what Sam was doing.

"Are you seriously going to wash your clothes? They are just rags Sam, and the more we wash them the sooner they will fall apart." He said when he saw his younger brother strip out of his clothes beside the water.

"We have walked through mud and dirt the entire day Dean, they are covered in shit. And I want to take a dip in the water anyway." Sam said while he took off his shirt and walked into the stream, to a spot where the water was deep enough to reach him to the chest. Dean had to look away when he looked at Sam's naked body, it was almost two months ago since the assault and the wounds on the body had mostly healed, but Dean still couldn't look at him without feeling responsible. After his face, Sam's chest and back looked the worst, there had been deep cuts there, and they had left deep scars, the red lines stood out against the tanned skin.

"Hey!" Sam shouted and splashed cold water at Dean. "You need a dip too, I can smell your stink from here. And you're covered in mud, jerk." Sam teased with a smile.

"Fine, whatever, bitch. But I know it's only an excuse to see me naked again." Dean said with a wink, and laughed when he saw Sam shudder.

"Yeah right, because all I think about is new excuses to see my brother naked. If I had to see you walk around naked all the time, I swear, I would have cut out my other eye too in the end."

"Aww, Sammy, that hurts!" Dean mocked while he stepped out of his grimy clothes and joined his brother in the cold water. He was glad Sam was able to joke about his scars now, it had been a sensitive subject for a long time.

Dean had to admit, it felt good to wash off the dirt and sweat, and after they both had rinsed their clothes they stayed in the cold water while the clothes dried in the sun. Dean sat on a large rock, with water up to his neck, and relaxed completely for the first time in what felt like years. Sam was here beside him, scarred, one-eyed and maimed, but relaxed and happy, and they were both alive. Dean let his head lean back and felt all tension unwind from his body and mind, when Sam suddenly sat up, ready and alert, but for what he did not know.

"Sam! What's going on?" He whispered, and got up in a similar position.

"Shhh! I heard something. I think someone's here." Sam whispered, his eye drifting around their surroundings.

"You got a weapon?" Dean asked while he bent down and reached for the dagger he still had tied around his leg. He never took it off. Sam nodded and showed him the small knife he had in his hand. They both stood there tense and ready, listening for any signs of intruders for a few minutes, before they looked at each other again.

"You sure you heard something? It could have been an animal..." Dean asked hesitantly. He hoped it was nothing, but after the last months, they took no chances.

"I thought I did... It sounded like a twig snapping or something. But we are in the woods, so I guess it could have been an animal. Let's get dressed and get out of here." Sam said and started to climb out of the water. Dean followed slowly, with his dagger still ready and with wary eyes follow the surroundings. He couldn't see anything suspicious, and there weren't many places to hide if Henriksen had found them. He saw Sam probably think the same, with a small laugh and shake of his head Sam tied the knife back to his leg.

"Guess there was nothing. Can't blame me for being paranoid though, after the last few months we have been through. Every little sound makes me ready for a fight." Sam said with a weak and tired smile that Dean returned while he too tied his knife back in place around his leg.

"I hear ya, every time I start to relax and believe we might finally get away from all the crap that follows us, the shoe always seem to drop." Dean said with a sigh and reached for his clothes. They were not completely dry yet, but he put them on anyway, he didn't want to risk staying here any longer. Something didn't feel right about this place, even if no one had approached or attacked them it felt like they were being watched.

After they both were dressed Dean shot a last suspicious glance around them, but came up empty. He huffed and was about to give another snarky comment to Sam about how paranoid they acted when the first arrow shot through the air.


	3. Chapter 3

Yet again, the other shoe had dropped.

Of course, with the Winchester brothers it always did. When they had stood in that open clearing by the stream, and were about to leave, the attack had started. But it didn't last long, after all it's not easy to fight against arrows with daggers and knives, especially when they couldn't even see their attackers. The only choice they had was to get the hell out of there, to run like they always did, but that was where their problem started. The arrows that had shot down all around them, wasn't shot to kill, they had heavy nets strapped to them that effectively managed to pin the both of them to the ground. They were trapped.

"Crap!" Dean grunted, and tried to squirm so he could reach down to his foot and grab the dagger he had been stupid enough to pack away, but the nets were to heavy and held him securely in place.

"Guess you did hear something then, huh?" he tried to joke even if they were in a really bad situation now, trapped like animals.

"Not the time, Dean!" Sam hissed, and they both tensed when they heard several footsteps come closer, and men laughing and talking in a language Dean didn't understand. Not Henriksen then, he thought, but didn't know whether he should be relieved or scared. At least, with Henriksen he knew what to expect. Some crappy monologue about what a horrible person Dean is and how he will burn in Hell for the rest of eternity, and then a quick death. Now though… He had no idea.

The footsteps came closer, and finally into his line of vision. Six guys dressedin black, that's three for Dean and three for Sam, they could manage to take them down. Had been up against larger groups before, but then they usually were armed or the other people were drunk. Now though, they didn't exactly have the upper hand. These guys were large, young and armed.

What looked to be the leader, a dark haired man around fourty, crouched down between them while the other five stood in a circle around them, ready with ropes in their hands. Two of the men lifted up the net over Dean's legs and he tried to kick, but one of them pinned him effectively to the ground while the other quickly removed the dagger from his leg. Great, unarmed and trapped against six guys. When they took Sam's knife as well he looked at his brother, and knew they both were thinking the same thing. They were in deep shit. Again.

Xxx

"So what do you think they plan to do with us?" Dean asked his brother later, when they had been thoroughly tied up and placed in one of the wagons. The men that had captured them clearly didn't take any chances on letting them escape. They were tied around the wrists, around the ankles, their arms were tied around the chest, and they were tied to the wagon itself. Other than that they had been completely ignored after being placed in the back of a wagon, and the group had started moving again. They group had three wagons, each pulled by a horse, and with two men in front on each wagon.

"Well…" Sam started slowly while studying the rest of the content around them. "I would guess these guys are traders, judging by all the stuff they have with them. Like all the fabric and leather in this wagon. Thought I saw they had food in one of the others and weapons in the last. So they travel around and trades stuff. And really, what do you think travelling tradesmen do with captives?"

"Great, we're slaves. But at least we're still alive. I mean, had it been a certain someone else ambushing us back there we would have been dead already. As long as we're still alive we still have a chance to get away. We'll get through this." Dean said, and tried to sound confident and reassuring, even though he didn't feel it at all. They were screwed, and they both knew it. These guys were professional in capturing people, and probably wouldn't let them out of sight for even a second.

Xxx

The caravan traveled down the dirt road for several hours before they stopped for the night on a grass field. Dean could only watch as they prepared for the night, one guy made a bon fire, one unstrapped the horses from the wagons and tied them with a long rope to a tree on the clearing where they could stay for the night and grass. Two of them set up some cover for the night using large skins and sticks, and one guy prepared dinner, some kind of soup. The last one, a tall guy with scruffy blond hair was clearly on babysitting duty, he stood solemnly still and observing the brothers' every motion. Dean glared defiantly back at him, and received an amused smirk in return, but he didn't let it stop him.

After a few minutes he could hear what he thought was the leader shout something to their babysitter in the strange language from the campfire where the rest of the group now was seated eating their dinner. The babysitter shouted something back to him before he jumped up into the cart and walked over towards Dean. He untied the rope that had tied him to the wagon, and Dean had a small hope that he would untie more of them, but that was crushed when the babysitter dragged him out of the wagon with unexpected strength, and Dean landed hard on the ground, a sight that made the rest of the group break out in laughter.

Dean was unnerved when he realized this man was probably much stronger than him, and with a quick glance at the rest of the group he realized all of these men were not only taller and bulkier than him, but also taller and bulkier than Sam.

After being unceremoniously dropped on the ground Dean tried to stand up, something that wasn't easy when he was bound tight around his feet and arms, and the sound of laughter rose until the leader shouted something to the babysitter again. Then Dean was suddenly swept off his feet, and he realized he was being carried bridal style towards the group. He tried to squirm out of the grip, but to no avail.

When they reached the group Dean was placed on the ground between the leader and the babysitter, who received a bowl of the soup they were eating. Dean, who hadn't eaten anything other than some berries and apples for the last few days, and not much in the days before that either, felt his mouth watering and stomach growl with the smell of warm, tasteful food that actually had meat. Dean could almost not even remember the last time he and Sam had eaten meat. They had been too busy running and hiding too hunt proper food, and had instead eaten what they could find, or steal. Even if they had been innocent before the manhunt, they had been made into criminals during it, they had to if they wanted to survive.

The men could obvious see Dean's reaction to the food, and even if he hoped to get a bowl of soup, he knew he couldn't expect it. He was captured as a slave, and slaves were rarely treated well. Dean turned around and looked to the wagon were Sam still was bound. He didn't understand why only he was brought here and Sam was left on his own, while earlier they had both been under strict supervision. He hoped Sam took the opportunity to try to untie his ropes, if Sam got loose he could untie Dean, and they could maybe escape during the night.

Dean sat in his own thoughts, planning how they could escape that night, so focused that he didn't notice the smell of food coming closer until it was right under his nose. At first he stared at the spoon in disbelief, he had not expected them to actually give him food, he thought they had brought him here just to gloat. Then he understood what this action meant and glowered angry at the babysitter who held the spoon, still with that annoying smirk. He pressed the wooden spoon once again against Dean's closed lips, but he didn't react. He wanted food, but no way in Hell was he allowing them to feed him like a child.

The third time the spoon pressed against his lips without any reaction, the babysitter showed the first sign of anger.

"Eat." He said with a low voice.

"No." Dean answered defiantly, realizing too late what a failed move that was.

As soon as his mouth opened, the spoon rushed in, and Dean couldn't help but close his eyes when he tasted the warm and tasteful soup. When he opened them again it was to look into the triumphant smirk of the babysitter, who already had a new spoon ready. Dean was ready to refuse it again, but then he saw several large pieces of meat on the spoon and remembered how good it had tasted. And besides, if they were escaping tonight, he needed his strength. Dean swallowed his pride and opened his mouth up, ready for the man to push it in once again. But this time he just kept it in front of the lips, forcing Dean to lean forward and close his lips around it. It continued like this until the small bowl was empty, the man sometimes pushed the spoon inside Dean's mouth before he was ready, sometimes he held it just out of reach, so Dean had to lean forward, and a few times he moved it slowly against Dean's open mouth, only to suddenly take it for himself instead, and laugh when Dean glared at him. He really didn't like this smirking bastard.


	4. Chapter 4

When the bowl of soup was empty, Dean looked around the camp to see most of the men had retreated to the makeshift tents, all except two of them who now where guarding Sam, and the one who had fed Dean the soup. Crap, Dean thought, when he saw the new guards watching Sam. So much for escaping tonight.

Dean was suddenly yanked by his arm and hauled up to his feet by the babysitter's strong grip. He yelped in surprise, but managed to stay on his feet. He felt the man's arm sneak around his shoulders to support him, but he jumped away and glowered at him.

"I can walk by myself, you bastard." Dean growled and started towards the wagon and Sam. It wasn't easy with his ankles tightly bound, he used a combination of small steps and small jumps, and managed to get half the distance before he lost his balance and fell down on the grass. That produced a small chuckle from the man, who had stood with his arms crossed and his usual bemused expression and watched him. Now he walked over towards Dean and yanked him up again.

"I can see that. But I'm afraid you walked the wrong way." The man said with a small smile and pointed a finger in the right direction. Dean's face went deathly pale when he saw where the finger pointed and shook his head.

"No, no, no, not that. I mean, thanks for the food and all, but I don't put out on the first date." The man just continued to smile and threw his arm over Dean's shoulder. He turned his head and shouted something in that foreign language to the two men guarding Sam that sounded like a command, before he steered Dean around and started walking. Dean tried to struggle, but then the man spoke again in a low and dangerous voice.

"You might want to know what I just said to my friends over there. I told them that if I give the command to, they are to kill your friend. A quick slice over the throat, and he's gone. So you might want to be a good boy for me tonight if you want him to stay alive." The man whispered conspiratorially in Dean's ear while they walked across the grass field, and towards one of the small tents. The man pushed aside the leather and gestured for Dean to get inside. With a quick glance back to the wagon where Sam still was tied up, he saw the two guards with their knives ready smiling at him, and he crawled inside.

As soon as they were both inside the man wasted no time. He pushed Dean down into the furs used as bedding with one hand, while the other sneaked behind his back to reveal a large, silver dagger. Dean's breath hitched when the man used the sharp weapon to caress Dean's cheek and dragged it slowly down his cheekbone, and down his neck, scraping it gently enough against the skin that it hurt, but not enough to draw blood. When the dagger reached the hem of Dean's ragged shirt he put it in under the fabric, and Dean was afraid the man was going to kill him after all. Instead the dagger pointed upwards, tore through the fabric, and ripped open to reveal Dean's chest. Dean let out the breath he hadn't even noticed he had held in, when the man continued to cut through the shirt, until he could pluck the pieces of ruined fabric away to look at Dean's naked torso.

The man stopped to admire Dean's body for a few seconds, before he continued down, and used his dagger to cut away the pants, leaving Dean naked on the ground below him. Dean shuddered when he saw the heavy lust revealed in the man's eyes, and how he looked at him with a predatory smile. Like a wolf eyeing a big piece of bloody and fresh meat, ready to devour every last bit.

The man used one hand to untie his pants and pull them down, revealing a fully erected and leaking cock. Way too big for Dean's liking, especially when he knew where it probably would end up during the night. The man pushed Dean up and dragged his head into his lap, so that Dean lay face to face with tonight's enemy, and he felt it trying to push into his closed mouth.

"Come on baby, open up. I know you can, you were so good earlier tonight with the spoon. Open those beautiful lips for me." The man said and pushed one more time. Dean pinched his lips tighter together, but felt a strong hand grip tight in his short hair, and pull his head back until he was forced to look into the stormy blue eyes of the man.

"Remember, one word from me and your friend dies. We don't need him, he's one-eyed, ugly and damaged, won't get us any good money. Are you going to be a good boy for me, or do I have to talk to my friends?" The man said in a low threating voice. Dean closed his eyes and obediently opened his mouth.

The hand in his hair pushed his head down into the waiting lap again, and Dean felt tears prickle behind his eyes of shame when he took the man's erection into his mouth. He heard the man gasp when his lips closed around the flesh, then he felt the hand in his hair tighten his grip again to hold the head in place, while the man's hips started to buck, and thrust into Dean's mouth.

He tried to just lay still and take it, tried to focus on breathing through his nose while his mouth was violated, and let his mind wander, but he was disrupted by the man's grunts and commands.

"Come'on, baby use your tongue… Ah, slower… Yeah, just like that, such a good boy…"

Dean felt the man starting to tense and heard him breathing faster. Relieved that it would soon be over with just his mouth violated and nothing else, Dean continued using his tongue, trying to get it to be over faster. When he thought the man was on the point of climaxing the hand in his hair gripped tight, and he was violently pulled off the man's dick. He gasped and looked up to the man who grinned down at him and licked his lips slowly and predatorily.

"Thought it was almost over, didn't you? Oh, I'm not nearly done with you yet, boy." He said with a low and dark chuckle that made Dean shiver, before he was flipped over on his back.


	5. Chapter 5

Lying naked on the ground with his hands and feet tied and the larger man looming over him, Dean couldn't remember to ever feel so small and vulnerable before. But if it was something Dean Winchester was not, it was to be small and vulnerable. He was a tall, strong and skilled fighter and he had defeated men taller and stronger than him before. If only he could get his hands or feet free, he might be able to beat this one too in a fight and get away.

Dean hissed when he felt the cold metal of his captor's dagger once again travel slowly over his body, down from his shoulders, over his torso, and then down his legs where it ended up in the rope around his ankles. As the man started cutting through, Dean felt adrenalin pumping through his body and his heart beating faster. If he could get his feet free, and he managed to get a good kick in, he could knock the man out. Then he could use the dagger to cut free his hands, grab the man's clothes and sneak out into the night. When he reached the forest…

Dean stopped the way his thoughts were going when he remembered the other person trapped here with him. Sammy, the younger brother he had sworn to protect with his life since the day their father died, leaving the brothers alone in this world. Sammy, the tall and lanky kid who just after his eighteenth birthday had gone from being a boy with a shy smile and the cute dimples that several of the girls in their village had loved, to a cold and haunted man who had experienced real and true evil from the humans in this world.

His innocence was lost, but Sam hadn't simply lost it. It had been cut out of him with sharp knives, and disappeared along with his left eye, his blood and his tears while the man holding the blade had just smiled and laughed down at him while he enjoyed his work. Thinking back to that day, Dean knew he couldn't go through with his small escape plan. It was too risky and dangerous, and if it was one thing in this world Dean would never risk, it was Sam. The kid had been through enough during his short life.

The feeling of his free feet being moved brought Dean back to reality, and he looked down to see the still clothed man down on his knees and crawling closer, with Dean's legs over his shoulders. He stopped when their faces were inches apart, with one of his hands on each side of Dean's head. When Dean saw the man's lips coming closer he wanted to push him away, but his hands where still tied and now securely trapped between their bodies. Instead he squeezed his eyes and lips tightly together and turned his face to the left, pressing his left cheek hard down against the furs they were using as a bed. This didn't stop the man though, and Dean felt the man's lips place gentle kisses across his jaw. The lips ended up on Dean's own in a final kiss before the man pulled away.

The next thing Dean felt was a finger trying to push through his closed lips and into his mouth, but he only pinched them harder together. He had had enough disgusting things inside of his mouth for today, and wasn't willingly opening up for more.

"Open your mouth, pretty one. I need my fingers to be good and wet for the next part." The man murmured, before he sighed when Dean opened his eyes only to glare at him. Dean had an idea what the man was referring to as the next part, but fingers had nothing to do with that.

"Have you ever had sex with another man before?" The man asked him then, and sounded almost gentle. Dean slowly shook his head while he continued to glare at him. The man smiled then, before he started to explain.

"Well, sex between two men is a bit different than between a man and a woman. You will need a little preparation, so I am going to use my fingers to widen up your hole a bit so it won't hurt so much when I push my dick inside you. And it is easier to do when my fingers are wet." He said while putting two fingers against Dean's lips again. "Or I can just fuck you dry until you tear up inside, and we can use your blood as lubrication. It's your choice, my pretty little virgin."

Dean reluctantly opened up his mouth and let the fingers in, realizing that no matter what he did, the outcome was inevitable, so why not choose the less painful scenario. The man's fingers tasted like dirt and leather when he sucked on them, he could even taste smoke from the fire earlier that evening and a faint taste of the soup they had for dinner. He decided to cling to that flavor and not think about where else these fingers might have been since the last time they were washed.

"Oh God, you are beautiful using your mouth like that. " The man whispered, and Dean glanced up to see the man stare at him with heavily dilated blue eyes. "I swear I could come from just watching you. But that's not the plan for today. It's enough now baby, let's get you ready for me."

When the first finger breached his hole and started working him open Dean tensed his muscles and pressed his head down to the side again. As the second finger followed he let out a small whimper of pain and felt tears start to trickle behind his eyes. The man started kissing him again, small gentle kisses all over his face meant to calm him down.

"Shhh, relax baby, I know it hurts. Just calm down and relax, and it will be okay. I'll try to be gentle with you, but it always hurts the first time. Just calm down and let me take care of you, okay?" the man said in a soothing voice, and Dean tried to force himself to trust him and force the tension out of his body. Instead of thinking about the pain and the fingers probing inside him he tried to focus on his breathing. Dean drew in long breaths and after a while of heavy breathing his body finally started to listen to him. But then a third finger suddenly joined the others in his too tight hole, and the pain flared up again.

Dean could not understand how this was something men willingly did with each other, this was unnatural and his hole was clearly not designed for this kind of intrusion. And this was only the preparation, so the worst was yet to come. He focused on his breathing again, but could still feel the fingers working inside him. Thankfully what the man did seemed to work, after a while it didn't hurt so much and he was able to relax without thinking too much about it. It still felt weird, but it wasn't painful. And when the man withdrew his fingers he actually felt kinda empty. But he didn't stay empty for long, the man was quick to pull down his pants, and cover his erect dick in his own spit before he pushed it inside Dean's body.

Dean hissed in pain when the new limb entered him, but was once again calmed down by the man's soothing voice and gentle kisses. By the time the man started to thrust his hips he was relaxed again, at least until the man gave an especially hard thrust and a new sensation flared up inside him and made Dean gasp up in surprise.

"What the-" Dean said, but then the man pushed in again, hitting the spot again, and he unwillingly let out a small moan. As he continued thrusting, Dean was loath to see his own dick starting filling as the pain was replaced by unexpected pleasure.

"Found your spot, did I?" The man chuckled knowingly when he saw Dean's change of demeanor. "Don't worry, baby, I'll take care of you. My very own pretty little virgin, I'm going to make it good for you." He said and grabbed Dean's now fully erected dick, giving it a careless hand job.

Dean bit down hard at his bottom lip as he fought the pleasure now unfolding through him, but he was betrayed by his own body and let out several unwanted sounds through his closed lips. He wouldn't admit that the needy whimpers he produced were something his captor caused, but in the end he wasn't sure if the pleading look he sent the man was because he wanted him to stop or to continue. The other man clearly interpreted it as the latter as he sped up both the hard thrusts and the hand job. The pleasure was too much now, and Dean came hard, releasing his seed over his stomach and the man's hand, while simultaneously fighting the sounds trying to escape him by biting so hard at his lip he could taste blood in his mouth. The man followed him soon after, and Dean could feel the man's warm come filling him up inside before he was captured in a bruising kiss.

He was too tired to fight it this time, Dean let the man assault his mouth while the exhaustion from the long day took over, and he could vaguely feel strong arms close tight around him before he drifted off to sleep.


End file.
